[CH2:1]([O:6][CH2:7][C:8]#[C:9][CH2:10][OH:11])[CH2:2][CH2:3][CH2:4][CH3:5].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C=O>C(OCC)C.O>[CH3:19][S:20]([O:11][CH2:10][C:9]#[C:8][CH2:7][O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])(=[O:22])=[O:21]To a 300 mL 3 neck flask equipped with magnetic stirrer, addition funnel, and nitrogen inlet was charged 7.42 grams (g) of 4-(pentyloxy)but-2-yn-1-ol (0.45 mmol), 70 mL of dry ethyl ether, and 6.8 g (68 mmoles) of anhydrous triethyl amine The reaction mixture was cooled to 5° C. with stirring followed by the dropwise addition of 4.95 g (43 mmole) of methane sulfonyl chloride in 7 mls of ethyl ether. The temperature was adjusted to 0° C. and 5.4 g (180 mmole) of solid paraformaldehyde was added. The mixture was then stirred at 10-15° C. for 6 hours, then diluted with another 40 mls of ether and 70 mls of water. The organic phase was separated, and washed with water and brine, then dried over anhydrous magnesium sulfate. Filtered and concentrated under vacuum on a rotary evaporator. Isolated 9.5 g of a clear colorless liquid which was consistent with the desired structure upon analysis by 300 MHz 1H NMR.
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